 
data_shelx
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H16 N2 O3 S' 
_chemical_formula_weight          352.40

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    10.078(2)
_cell_length_b                    12.770(3)
_cell_length_c                    14.077(3)
_cell_angle_alpha                 90.00(3)
_cell_angle_beta                  107.55(3)
_cell_angle_gamma                 90.00(3)
_cell_volume                      1727.2(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     452
_cell_measurement_theta_min       2.720
_cell_measurement_theta_max       26.463
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.355          
_exptl_crystal_F_000              736
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.07
_exptl_crystal_size_min           0.05
_exptl_absorpt_coefficient_mu     0.208
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker P4'
_diffrn_measurement_method        'ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             21384
_diffrn_reflns_av_unetI/netI      0.0221
_diffrn_reflns_av_R_equivalents   0.0365
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          2.720
_diffrn_reflns_theta_max          26.463
_diffrn_reflns_theta_full         25.500
_diffrn_measured_fraction_theta_max   0.988
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.988
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.988
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3534
_reflns_number_gt                 2946
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0456P)²+0.4454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef        0.0107(11)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3534
_refine_ls_number_parameters      231
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0433
_refine_ls_R_factor_gt            0.0341
_refine_ls_wR_factor_ref          0.0965
_refine_ls_wR_factor_gt           0.0910
_refine_ls_goodness_of_fit_ref    1.037
_refine_ls_restrained_S_all       1.037
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.68974(4) 0.66180(3) 0.75375(3) 0.03991(13) Uani 1 1 d . . . . .
O1 O 0.68820(12) 0.59507(9) 0.83524(8) 0.0517(3) Uani 1 1 d . . . . .
O2 O 0.70622(13) 0.77268(9) 0.77119(9) 0.0588(3) Uani 1 1 d . . . . .
O3 O 0.30822(15) 0.36339(11) 0.72629(12) 0.0764(4) Uani 1 1 d . . . . .
N1 N 0.46112(14) 0.35006(10) 0.63921(11) 0.0461(3) Uani 1 1 d . . . . .
N2 N 0.35612(15) 0.16391(10) 0.56601(10) 0.0503(3) Uani 1 1 d . . . . .
C12 C 0.47339(14) 0.54445(11) 0.62697(10) 0.0358(3) Uani 1 1 d . . . . .
C7 C 0.53314(15) 0.64350(11) 0.65496(10) 0.0356(3) Uani 1 1 d . . . . .
C1 C 0.82521(15) 0.61934(12) 0.70745(11) 0.0419(3) Uani 1 1 d . . . . .
C15 C 0.29789(16) 0.21002(11) 0.62819(12) 0.0431(3) Uani 1 1 d . . . . .
C13 C 0.53722(16) 0.44434(11) 0.67979(12) 0.0447(4) Uani 1 1 d . . . . .
H13A H 0.6315 0.4380 0.6762 0.054 Uiso 1 1 calc R U . . .
H13B H 0.5426 0.4498 0.7496 0.054 Uiso 1 1 calc R U . . .
C14 C 0.35580(17) 0.31491(12) 0.66959(13) 0.0467(4) Uani 1 1 d . . . . .
C8 C 0.47239(18) 0.73396(12) 0.60568(12) 0.0483(4) Uani 1 1 d . . . . .
H8 H 0.5142 0.7986 0.6252 0.058 Uiso 1 1 calc R U . . .
C11 C 0.35142(16) 0.54160(13) 0.54771(11) 0.0450(4) Uani 1 1 d . . . . .
H11 H 0.3094 0.4773 0.5267 0.054 Uiso 1 1 calc R U . . .
C9 C 0.35043(19) 0.72810(14) 0.52804(13) 0.0550(4) Uani 1 1 d . . . . .
H9 H 0.3089 0.7886 0.4956 0.066 Uiso 1 1 calc R U . . .
C10 C 0.29088(17) 0.63175(15) 0.49921(12) 0.0526(4) Uani 1 1 d . . . . .
H10 H 0.2090 0.6272 0.4465 0.063 Uiso 1 1 calc R U . . .
C2 C 0.89572(17) 0.52756(13) 0.74218(13) 0.0522(4) Uani 1 1 d . . . . .
H2 H 0.8700 0.4867 0.7884 0.063 Uiso 1 1 calc R U . . .
C16 C 0.1904(2) 0.16605(15) 0.65611(15) 0.0619(5) Uani 1 1 d . . . . .
H16 H 0.1519 0.2010 0.6995 0.074 Uiso 1 1 calc R U . . .
C19 C 0.3051(2) 0.07035(15) 0.53033(15) 0.0642(5) Uani 1 1 d . . . . .
H19 H 0.3440 0.0368 0.4865 0.077 Uiso 1 1 calc R U . . .
C6 C 0.8611(2) 0.68061(17) 0.63861(14) 0.0649(5) Uani 1 1 d . . . . .
H6 H 0.8139 0.7426 0.6156 0.078 Uiso 1 1 calc R U . . .
C3 C 1.00413(19) 0.49670(17) 0.70820(16) 0.0681(5) Uani 1 1 d . . . . .
H3 H 1.0527 0.4354 0.7318 0.082 Uiso 1 1 calc R U . . .
C18 C 0.1989(2) 0.02091(16) 0.55440(17) 0.0717(6) Uani 1 1 d . . . . .
H18 H 0.1672 -0.0443 0.5275 0.086 Uiso 1 1 calc R U . . .
C17 C 0.1410(2) 0.06889(16) 0.61817(18) 0.0739(6) Uani 1 1 d . . . . .
H17 H 0.0692 0.0369 0.6361 0.089 Uiso 1 1 calc R U . . .
C4 C 1.0396(2) 0.5564(2) 0.63993(19) 0.0825(7) Uani 1 1 d . . . . .
H4 H 1.1127 0.5355 0.6168 0.099 Uiso 1 1 calc R U . . .
C5 C 0.9695(3) 0.6474(2) 0.60447(19) 0.0881(7) Uani 1 1 d . . . . .
H5 H 0.9949 0.6869 0.5572 0.106 Uiso 1 1 calc R U . . .
H1A H 0.4897(18) 0.3118(14) 0.6033(13) 0.048(5) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O1 1.4328(12) . ?
S1 O2 1.4381(12) . ?
S1 C1 1.7661(16) . ?
S1 C7 1.7764(16) . ?
O3 C14 1.217(2) . ?
N1 C14 1.336(2) . ?
N1 C13 1.4490(19) . ?
N1 H1A 0.815(18) . ?
N2 C15 1.329(2) . ?
N2 C19 1.337(2) . ?
C12 C11 1.389(2) . ?
C12 C7 1.4052(19) . ?
C12 C13 1.521(2) . ?
C7 C8 1.391(2) . ?
C1 C6 1.376(2) . ?
C1 C2 1.381(2) . ?
C15 C16 1.379(2) . ?
C15 C14 1.506(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C8 C9 1.379(2) . ?
C8 H8 0.9300 . ?
C11 C10 1.383(2) . ?
C11 H11 0.9300 . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C19 C18 1.370(3) . ?
C19 H19 0.9300 . ?
C6 C5 1.386(3) . ?
C6 H6 0.9300 . ?
C3 C4 1.357(3) . ?
C3 H3 0.9300 . ?
C18 C17 1.356(3) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O1 S1 O2 118.51(7) . . ?
O1 S1 C1 108.00(8) . . ?
O2 S1 C1 107.63(8) . . ?
O1 S1 C7 109.08(7) . . ?
O2 S1 C7 107.02(8) . . ?
C1 S1 C7 105.90(7) . . ?
C14 N1 C13 122.02(14) . . ?
C14 N1 H1A 117.4(12) . . ?
C13 N1 H1A 119.9(12) . . ?
C15 N2 C19 116.54(15) . . ?
C11 C12 C7 116.70(14) . . ?
C11 C12 C13 120.80(13) . . ?
C7 C12 C13 122.50(13) . . ?
C8 C7 C12 121.39(14) . . ?
C8 C7 S1 115.77(11) . . ?
C12 C7 S1 122.84(11) . . ?
C6 C1 C2 121.02(16) . . ?
C6 C1 S1 118.81(14) . . ?
C2 C1 S1 120.15(13) . . ?
N2 C15 C16 123.24(15) . . ?
N2 C15 C14 116.88(14) . . ?
C16 C15 C14 119.87(15) . . ?
N1 C13 C12 114.21(13) . . ?
N1 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
N1 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
O3 C14 N1 123.18(15) . . ?
O3 C14 C15 121.52(15) . . ?
N1 C14 C15 115.31(14) . . ?
C9 C8 C7 120.23(15) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C11 C12 121.77(15) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C10 C9 C8 119.20(15) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 120.71(15) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C3 C2 C1 119.85(18) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C15 C16 C17 118.53(18) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N2 C19 C18 124.02(19) . . ?
N2 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C17 C18 C19 118.68(18) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C17 C16 118.98(18) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
 
_refine_diff_density_max    0.277
_refine_diff_density_min   -0.250
_refine_diff_density_rms    0.034



